PL109305B2 - Method of obtaining new acid dyes-anthraquinone derivatives - Google Patents
Method of obtaining new acid dyes-anthraquinone derivatives Download PDFInfo
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- PL109305B2 PL109305B2 PL20945478A PL20945478A PL109305B2 PL 109305 B2 PL109305 B2 PL 109305B2 PL 20945478 A PL20945478 A PL 20945478A PL 20945478 A PL20945478 A PL 20945478A PL 109305 B2 PL109305 B2 PL 109305B2
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- hydrogen atom
- group
- parts
- methyl
- alkali
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- 238000000034 method Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 title description 5
- QZZSAWGVHXXMID-UHFFFAOYSA-N 1-amino-4-bromo-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=C(Br)C=C(S(O)(=O)=O)C(N)=C3C(=O)C2=C1 QZZSAWGVHXXMID-UHFFFAOYSA-N 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 claims description 2
- 239000000980 acid dye Substances 0.000 claims description 2
- 239000001099 ammonium carbonate Substances 0.000 claims description 2
- 235000012501 ammonium carbonate Nutrition 0.000 claims description 2
- 239000000908 ammonium hydroxide Substances 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 150000004679 hydroxides Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- -1 nitro, sulfo, methyl Chemical group 0.000 claims 3
- 229910052783 alkali metal Chemical group 0.000 claims 2
- 150000001340 alkali metals Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 229910052784 alkaline earth metal Chemical group 0.000 claims 1
- 150000001342 alkaline earth metals Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims 1
- 150000004056 anthraquinones Chemical class 0.000 claims 1
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 150000001879 copper Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 101150050740 ino1 gene Proteins 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 125000001174 sulfone group Chemical group 0.000 claims 1
- 239000000975 dye Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000010985 leather Substances 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000012254 magnesium hydroxide Nutrition 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical class [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
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Description
Opis patentowy opublikowano: 30.04.19812 109 305 skóre, przy czym otrzymane wybarwienia charakteryzuja sie wybitnymi odpornosciami na swiatlo i czynniki mokre bez dodatkowych operacji utrwalajacych.Wynalazek ilustruja nie ograniczajac jego zakresu nastepujace przyklady, w których czesci i procenty oznaczaja czesci i procenty wagowe, a stopnie temperatury sa podane w skali Celsjusza: Przyklad I. Do mieszaniny skladajacej sie z 62,5 czesci 1-amino-2-sulfo-4-bromoantrachinonu, 200 czesci wody i 55,7 czesci kwasu 4-amino-4'-nitrodwufenyloamino-2'-karboksylowego podgrzanej do temperatury 30° dodaje sie 84 czesci kwasnego weglanu sodu, a nastepnie otrzymana mieszanine podgrzewa sie do temperatury 80°, dodaje roztwór zawierajacy 10 czesci siarczanu miedziowego oraz 100 czesci wody i calosc wygrzewa sie w temperaturze 80—90°C przez 15—20 minut. Po zakonczonym ogrzewaniu barwnik wydziela sie przez wysolenie 15 czesciami chlorku sodu i odfiltrowanie w temperaturze 80°. Otrzymany osad przemywa sie 2% kwasem solnym i suszy uzyskujac 100 czesci barwnika barwiacego wlókna poliamidowe i proteinowe oraz skóre na kolor zielony Zamiast kwasnego weglanu sodu mozna stosowac równowazne ilosci wodorotlenku lub weglanu amonu badz weglanów, tlenków lub wodorotlenków sodowego, potasowego, litowego lub magnezowego.Przyklad II. 70 czesci suchego barwnika otrzymanego w przykladzie I zawiesza sie w 300 czesciach alkoholu butylowego i nastepnie w temperaturze nie przekraczajacej 30° dodaje sie wciagu 1 godziny 17 czesci chlorku tionylu po czym calosc miesza sie w temperaturze 70—75° w ciagu 4 godzin celem zakonczenia estryfikacji. Otrzymany barwnik wydziela sie przez wylanie na 10% solanke i odsaczenie. Po wysuszeniu otrzymuje sie 76 czesci barwnika barwiacego wlókna poliamidowe, proteinowe, poliestrowe i skóre na kolor zielony.P r z y k la d III. Do mieszaniny skladajacej sie z 62,5 czesci 1-amino-2-sulfo-4-bromoantrachinonu, 200 czesci wody i 560 czesci kwasu 4-amino-2'-nitro-4'-karboksylowego podgrzanej do 40° dodaje sie 90 czesci tlenku magnezu, a nastepnie otrzymana mieszanine podgrzewa sie do temperatury 80° i dodaje roztwór zawierajacy 5 czesci chlorku miedziowego oraz 20 czesci 3% kwasu solnego i calosc ogrzewa w temperaturze 70—80° przez 1 godzine. Po zakonczeniu ogrzewania barwnik wydziela sie przez wykwaszenie 100 czesciami kwasu solnego 30% i odfiltrowanie w temperaturze 40°. Otrzymany osad przemywa sie 2% kwasem solnym otrzymujac 105 czesci barwnika barwiacego wlókna poliamidowe, proteinowe oraz skóre na kolor oliwkowy.Postepujac sposobem opisanym w przykladzie I—III przy stosowaniu zamiast kwasu 4-amino-4'-nitro-dwu- fenyloamino-2'- karboksylowego innych pochodnych dwufenyloaminy o ogólnym wzorze 2, w którym symbole i miejsca podstawienia zostaly zamieszczone w ponizszej tabeli, otrzymuje sie szereg barwników kwasowych o ponizej podanych barwach. PLThe patent description was published: April 30, 19812 109 305 leather, the obtained dyes are characterized by outstanding resistance to light and wet agents without any additional fixing operations. The invention is illustrated without limiting its scope by the following examples, in which parts and percentages mean parts and percentages by weight, and degrees of temperature are given in the Celsius scale: Example I. A mixture consisting of 62.5 parts of 1-amino-2-sulfo-4-bromoanthraquinone, 200 parts of water and 55.7 parts of 4-amino-4'-nitrodiphenylamino-acid 2'-carboxylate heated to 30 °, 84 parts of acid sodium carbonate are added, then the resulting mixture is heated to 80 °, a solution containing 10 parts of copper sulphate and 100 parts of water is added and the whole is heated at 80-90 ° C for 15-20 minutes. After heating has ended, the dye is separated by salting out with 15 parts of sodium chloride and filtering at 80 °. The obtained precipitate is washed with 2% hydrochloric acid and dried to obtain 100 parts of a dye that dyes polyamide and protein fibers and the skin turns green. Instead of acid sodium carbonate, you can use equivalent amounts of ammonium hydroxide or carbonate or carbonates, sodium, potassium, lithium or magnesium oxides or hydroxides. Example II. 70 parts of the dry dye obtained in Example I are suspended in 300 parts of butyl alcohol, and then 17 parts of thionyl chloride are added for 1 hour at a temperature not exceeding 30 °, and the whole is stirred at 70-75 ° for 4 hours to complete the esterification . The dye obtained is separated by pouring into 10% brine and filtering. After drying, 76 parts of a dye that dyes polyamide, protein, polyester and leather green are obtained. Fig. III. To a mixture consisting of 62.5 parts of 1-amino-2-sulfo-4-bromoanthraquinone, 200 parts of water and 560 parts of 4-amino-2'-nitro-4'-carboxylic acid heated to 40 °, 90 parts of oxide are added magnesium, then the mixture obtained is heated to 80 ° C and a solution containing 5 parts of cupric chloride and 20 parts of 3% hydrochloric acid is added and the whole is heated at 70-80 ° for 1 hour. After the heating has ended, the dye is separated by acidification with 100 parts of 30% hydrochloric acid and filtration at 40 °. The precipitate obtained is washed with 2% hydrochloric acid to obtain 105 parts of a dye that dyes polyamide, protein and olive-colored leather. Following the procedure described in example I-III, using instead of 4-amino-4'-nitro-diphenylamino-2 'acid - carboxylic acid of other diphenylamine derivatives of general formula II, in which the symbols and places of substitution are shown in the table below, a series of acid dyes with the colors indicated below are obtained. PL
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL20945478A PL109305B2 (en) | 1978-09-06 | 1978-09-06 | Method of obtaining new acid dyes-anthraquinone derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL20945478A PL109305B2 (en) | 1978-09-06 | 1978-09-06 | Method of obtaining new acid dyes-anthraquinone derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL209454A1 PL209454A1 (en) | 1979-07-16 |
| PL109305B2 true PL109305B2 (en) | 1980-05-31 |
Family
ID=19991366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL20945478A PL109305B2 (en) | 1978-09-06 | 1978-09-06 | Method of obtaining new acid dyes-anthraquinone derivatives |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL109305B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2129653B1 (en) * | 2007-03-08 | 2017-05-17 | Rheinische Friedrich-Wilhelms-Universität Bonn | Novel p2y12 receptor antagonists |
-
1978
- 1978-09-06 PL PL20945478A patent/PL109305B2/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2129653B1 (en) * | 2007-03-08 | 2017-05-17 | Rheinische Friedrich-Wilhelms-Universität Bonn | Novel p2y12 receptor antagonists |
Also Published As
| Publication number | Publication date |
|---|---|
| PL209454A1 (en) | 1979-07-16 |
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